Sodium Chloride → (3,5-Difluoropyridin-4-yl)methanol

HRID 1844182Notes

Reaction equation

HRID 1844182 reaction equation
[F:1][C:2]1[CH:9]=[N:8][CH:7]=[C:6]([F:10])[C:3]=1[CH:4]=[O:5].[BH4-].[Na+].[Cl-].[Na+]>CO>[F:10][C:6]1[CH:7]=[N:8][CH:9]=[C:2]([F:1])[C:3]=1[CH2:4][OH:5]

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 4311764Sodium borohydrideHCID 116511703,5-Difluoropyridine-4-carbaldehyde

Product 1

HCID 66815317(3,5-Difluoropyridin-4-yl)methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

At RT, 11.60 g of 3,5-difluoroisonicotinaldehyde (Example 113A, 81 mmol, 1 equivalent), dissolved in 100 ml of methanol, were added to 3.68 g of sodium borohydride (97.3 mmol, 1.2 equivalent) in 200 ml of methanol. After the evolution of gas had ceased (about 2 h), 200 ml of saturated aqueous sodium chloride solution were added and the mixture was extracted twice with in each case 200 ml of ethyl acetate. The combined organic phases were dried over sodium sulphate and concentrated. This gave 9.5 g (81% of theory) of the title compound.

Workup

  1. additionwere added
  2. extractionthe mixture was extracted twice with in each case 200 ml of ethyl acetate
  3. dry with materialThe combined organic phases were dried over sodium sulphate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-bdbfea4f46124389ac316acad40e6343
Source dataset
uspto-grants-2015_02
Patent number
US08946215B2

Reaction notes

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